Dimension for weed control cannot be applied until the turf is "well-established"...its not for new seed.
I don't see how a power rake would deal with the drainage. Use the skid steer to slope the ground away from the house. On a big property a surveyor's transit or laser leveling setup would be helpful. Use plastic tile as needed.
Did you plan to kill the old grass first...or just major overseed? Mow short as you can and power rake; rake off the dead grass residue. Add starter fertilizer and seed. Use more than the usual amount of seed if you don't have irrigation or if conditions are less than perfect. Say maybe 10 pounds per thousand sqft. You may wish to drag the soil a couple of passes to get that all important SEED-TO-SOIL-CONTACT. Use the dead grass as straw to help hold moisture if you wish.
Start when temps fall under 85 degrees; start 8 weeks before frost--at least 6 weeks. Seed germinates quick in warm soil--if it is moist. Make sure the tall fescue is high quality--and that it claims to be disease resistant.
It claims brown patch resistance: